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Phytochemical Investigation on Some Species from the Genera Elettariopsis and Etlingera Yasodha Sivasothy Universiti Sains Malaysia 2008

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Phytochemical Investigation on Some Species from the Genera Elettariopsis and Etlingera Yasodha Sivasothy Universiti Sains Malaysia 2008 PHYTOCHEMICAL INVESTIGATION ON SOME SPECIES FROM THE GENERA ELETTARIOPSIS AND ETLINGERA YASODHA SIVASOTHY UNIVERSITI SAINS MALAYSIA 2008 PHYTOCHEMICAL INVESTIGATION ON SOME SPECIES FROM THE GENERA ELETTARIOPSIS AND ETLINGERA by YASODHA SIVASOTHY Thesis submitted in fulfillment of the requirements for the Degree of Doctor of Philosophy MAY 2008 ACKNOWLEDGEMENT Firstly, I would like to take this opportunity to thank my supervisor, Assoc. Prof. Dr. Wong Keng Chong for his advice and guidance. I am also thankful to my co-supervisor, Prof. Dr. Boey Peng Lim for his encouragement and helpful suggestions throughout the course of this study. Next, I would like to acknowledge the Dean of the Institute of Graduate Studies (IPS) for giving me a chance to pursue my postgraduate studies in USM. Special thanks to the Dean of the School of Chemical Sciences, Prof. Dr. Wan Ahmad Kamil Mahmood for providing me with the assistance and facilities which ensured the success of my research. I would also like to thank Institut Pengajian Siswazah for awarding me with the Graduate Assistant Scheme which covered my allowance and my tuition fee. I am very grateful to Datuk Lim Chong Keat from FRIM and Mr. Baharuddin Sulaiman from the School of Biological Sciences, USM for providing me with the plant materials and in the identification of them for my research. I would also like to thank Mr. Shanmugam from the School of Biological Sciences, USM for helping me prepare the voucher specimens for certain of those species. I would like to forward my appreciation to the technical and laboratory staffs of the School of Chemical Sciences, in particular, Mr. Chow Cheng Por, Mr. Clement D’Silva, Mr. Tan Chin Tong, Mr. Megat Hasnul, Mr. Yee Chin Leng, Mr. Chee Sai Gnow, Mr. Aw Yeong and Mr. Mohd. Fahmi Mohd. Yusoff for their assistance during the duration of this study. ii I would like to acknowledge Mr. Khoo Kay Hock and Mr. Hilman from the Centre for Drug Research, USM for their help with the GC-MS analyses. Special thanks to Madam Wong Lai Kwai and Madam Han Yan Hui from the Department of Chemistry, National University of Singapore for their help with the DP-MS and the NMR analyses. I would also like to thank my colleagues and friends for their cooperation and moral support throughout this project. Finally, I would like to convey my deepest gratitude to my parents for their love and encouragement. iii TABLE OF CONTENTS Page Acknowledgement ii Table of Contents iv List of Tables viii List of Figures xi List of Schemes xvi List of Abbreviations xvii List of Appendices xix Abstrak xxii Abstract xxiv CHAPTER ONE: INTRODUCTION 1 1.1 Natural Products Chemistry 1 1.2 The Zingiberaceae Family 1 1.2.1 The Origin of the Word ‘Ginger’ 1 1.2.2 Habitat 1 1.2.3 Distribution 2 1.2.4 Use and Commercial Importance 2 1.2.5 The Genus Elettariopsis 4 1.2.6 The Genus Etlingera 9 1.2.7 Previous Phytochemical Investigations 12 1.2.7.1 The Genus Elettariopsis 12 1.2.7.2 The Genus Etlingera 12 1.3 Research Objectives 13 1.3.1 Part 1 13 1.3.2 Part 2 14 iv CHAPTER TWO: MATERIALS AND METHODS 15 2.1 Collection of the Plant Materials 15 2.2 Chemicals and Reagents 15 2.3 Isolation and Analysis of Essential Oils 16 2.3.1 Isolation of Essential Oils 16 2.3.2 Chromatographic Analysis of the Essential Oils 18 2.3.2.1 Gas Chromatography 18 2.3.2.2 Gas Chromatography-Mass Spectrometry 20 2.3.3 Identification of the Essential Oil Components 20 2.3.4 Determination of Oil Yield 20 2.4 Isolation and Characterization of the Non-Volatile Constituents in the 21 Leaves, Fruits, Rhizomes and Roots of Etlingera littoralis 2.4.1 Extraction Procedure 21 2.4.1.1 Leaves 21 2.4.1.2 Fruits 21 2.4.1.3 Rhizomes and Roots 21 2.4.2 Separation Techniques 22 2.4.2.1 Thin Layer Chromatography 22 2.4.2.2 Column Chromatography 22 2.4.2.3 Preparative Thin Layer Chromatography 22 2.4.3 Isolation and Purification 23 2.4.3.1 Leaves 23 2.4.3.1.1 Petroleum Ether Extract 23 2.4.3.2 Fruits 24 2.4.3.2.1 Ethyl Acetate Extract 24 2.4.3.2.2 Petroleum Ether Extract 24 2.4.3.3 Rhizomes and Roots 25 v 2.4.3.3.1 Ethyl Acetate Extract 25 2.4.3.3.2 Petroleum Ether Extract 27 2.4.4 Structure Elucidation of Isolated Compounds 28 2.4.4.1 Melting Point 28 2.4.4.2 Infrared Spectroscopy 28 2.4.4.3 Gas Chromatography-Mass Spectrometry 28 2.4.4.4 Direct Probe-Mass Spectrometry 29 2.4.4.5 Nuclear Magnetic Resonance Spectroscopy 29 2.4.4.6 Ultra-Violet Spectroscopy (UV) of F1 29 2.4.4.6.1 Preparation of the Stock Solution of F1 30 2.4.4.6.2 Preparation of the Shift Reagent Stock Solutions and Solids 30 2.4.4.6.3 Steps in the UV Spectral Analysis of F1 30 2.4.4.7 Ultra-Violet Spectroscopy (UV) of L1, F2 and R4 31 2.4.4.8 Optical Rotation 31 CHAPTER THREE: RESULTS AND DISCUSSION 32 3.1 Essential Oil Analysis 32 3.1.1 Percentage Yield of Essential Oil 32 3.1.2 Chemical Composition of the Various Essential Oils 32 3.1.2.1 Essential Oils of Elettariopsis smithiae 33 3.1.2.2 Essential Oils of Elettariopsis rugosa 37 3.1.2.3 Essential Oils of Elettariopsis elan 41 3.1.2.4 Essential Oils of Elettariopsis slahmong 45 3.1.2.5 Essential Oils of Elettariopsis triloba 48 3.1.2.6 Essential Oils of Elettariopsis curtisii 52 vi 3.1.2.7 Significance of the Essential Oils in the Chemotaxonomic 56 Studies of the Genus Elettariopsis 3.1.2.8 Essential Oils of Etlingera littoralis 64 3.1.2.9 Essential Oils of Etlingera elatior and Etlingera elatior var. 68 Thai queen 3.2 Non-volatile Constituents Isolated from the Leaves, Fruits, Rhizomes and 75 Roots of Etlingera littoralis 3.2.1 Leaves 75 3.2.1.1 L1 75 3.2.1.2 L2 87 3.2.2 Fruits 107 3.2.2.1 F1 107 3.2.2.2 F2 122 3.2.3 Rhizomes and Roots 138 3.2.3.1 R1 138 3.2.3.2 R2 153 3.2.3.3 R3 168 3.2.3.4 R4 178 3.2.3.5 R5 185 CHAPTER FOUR: CONCLUSION 204 REFERENCES 206 APPENDICES 216 LIST OF PUBLICATIONS 234 vii LIST OF TABLES Page Table 2.1: Weight of Plant Material and Volume of Distilled Water Used for 17 Hydrodistillation Table 3.1: Percentage Yields of the Essential Oils of the Various Ginger Species 32 Table 3.2: Constituents of the Essential Oils of the Leaves and Roots of 34 Elettariopsis smithiae Table 3.3: Percentages of the Various Chemical Classes in the Essential Oils of 36 the Leaves and Roots of Elettariopsis smithiae Table 3.4: Constituents of the Essential Oils of the Leaves and Roots of 38 Elettariopsis rugosa Table 3.5: Percentages of the Various Chemical Classes in the Essential Oils of 40 the Leaves and Roots of Elettariopsis rugosa Table 3.6: Constituents of the Essential Oils of the Leaves and Roots of 42 Elettariopsis elan Table 3.7: Percentages of the Various Chemical Classes in the Essential Oils of 44 the Leaves and Roots of Elettariopsis elan Table 3.8: Constituents of the Essential Oils of the Leaves and Roots of 46 Elettariopsis slahmong Table 3.9: Percentages of the Various Chemical Classes in the Essential Oils of 47 the Leaves and Roots of Elettariopsis slahmong Table 3.10: Constituents of the Essential Oils of the Leaves and Roots of 49 Elettariopsis triloba Table 3.11: Percentages of the Various Chemical Classes in the Essential Oils of 51 the Leaves and Roots of Elettariopsis triloba Table 3.12: Constituents of the Essential Oils of the Leaves and Roots of 53 Elettariopsis curtisii Table 3.13: Percentages of the Various Chemical Classes in the Essential Oils of 55 the Leaves and Roots of Elettariopsis curtisii Table 3.14: Composition of the Essential Oils Isolated from Six Elettariopsis 59 Species Table 3.15: Constituents of the Essential Oils of the Leaves, Rhizomes and 65 Roots of Etlingera littoralis Table 3.16: Percentages of the Various Chemical Classes in the Essential Oils of 67 the Leaves, Rhizomes and Roots of Etlingera littoralis viii Table 3.17: Constituents of the Essential Oils of the Leaves, Rhizomes and 71 Roots of Etlingera elatior and Etlingera elatior var. Thai queen Table 3.18: Percentages of the Various Chemical Classes in the Essential Oils of 73 the Leaves, Rhizomes and Roots of Etlingera elatior Table 3.19: Percentages of the Various Chemical Classes in the Essential Oils of 74 the Leaves, Rhizomes and Roots of Etlingera elatior var. Thai queen 1 1 1 Table 3.20: H NMR (δppm) Assignments and H- H COSY Correlations of L1 in 82 CDCl3, 400 MHz 13 1 13 1 13 Table 3.21: C NMR (δppm) Assignments and H- C HMQC and H- C HMBC 83 Correlations of L1 in CDCl3, 75 MHz 1 1 1 Table 3.22: H NMR (δppm) Assignments and H- H COSY Correlations of L2 in 98 CDCl3, 400 MHz 13 1 13 1 13 Table 3.23: C NMR (δppm) Assignments and H- C HMQC and H- C HMBC 99 Correlations of L2 in CDCl3, 75 MHz Table 3.24: Important 1H-1H NOESY and 1H-1H ROESY Correlations of L2 in 105 CDCl3, 500 MHz Table 3.25: UV analysis of F1 in MeOH and the Effects of the Various Shift 107 Reagents 1 1 1 Table 3.26: H NMR (δppm) Assignments and H- H COSY Correlations of F1 in 120 CD3OD, 400 MHz 13 1 13 1 13 Table 3.27: C NMR (δppm) Assignments and H- C HMQC and H- C HMBC 120 Correlations of F1 in CD3OD, 75 MHz Table 3.28: Optical Rotations and Melting Points of Naturally Occurring 121 Catechins (Dictionary of Natural Products, 1996) Table 3.29: IR Spectral Data of F2 132 1 1 1 Table 3.30: H NMR (δppm) Assignments and H- H COSY Correlations of F2 in 133 CDCl3, 400 MHz 13 1 13 1 13 Table 3.31: C NMR (δppm) Assignments and H- C HMQC and H- C 134 HMBC Correlations of F2 in CDCl3, 75 MHz Table 3.32: IR Spectral Data of R1 147 1 1 1 Table 3.33: H NMR (δppm) Assignments and H- H COSY Correlations of R1 in 148 CDCl3, 400 MHz 13 1 13 1 13 Table 3.34: C NMR (δppm) Assignments and H- C HMQC and H- C 149 HMBC Correlations of R1 in CDCl3,
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